2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-3-oxa-9-deoxy-9,10-didehydro-PGD1 compounds

ABSTRACT

This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

The present application is a divisional application of Ser. No. 647,363, filed Jan. 8, 1976, now issued as U.S. Pat. No. 4,028,419.

The present invention relates to prostaglandin analogs for which the essential material consistuting a disclosure therefore is incorporated by reference here from U.S. Pat. No. 4,028,419. 

I claim:
 1. A prostaglandin analog of the formula ##STR1## wherein Y is trans-CH═CH-; wherein M₁ is ##STR2## or ##STR3## wherein R₅ is hydrogen or methyl; wherein L₁ is ##STR4## or a mixture of ##STR5## and ##STR6## wherein R₃ and R₄ are hydrogen, methyl, or fluoro, the same or different, with the proviso that one of R₃ andR₄ is methyl only when the other is hydrogen or methyl; Wherein g is one, 2, or 3; and wherein m is one to 5, inclusive.
 2. A compound according to claim 1, wherein m is one or
 2. 3. A compound according to claim 1, wherein m is 4 or
 5. 4. A compound according to claim 1, wherein m is
 3. 5. A compound according to claim 4, wherein g is one.
 6. A compound according to claim 5, wherein at least one of R₃ and R₄ is fluoro.
 7. A compound according to claim 6, wherein R₃ and R₄ are both fluoro.
 8. A compound according to claim 7, wherein R₅ is hydrogen.
 9. 2-Decarboxy-2-hydroxymethyl-16,16- difluoro-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-9- deoxy-9,10-didehydro-PGD₁, a compound according to claim
 8. 10. 2-Decarboxy-2-hydroxymethyl-16,16- difluoro-15-epi-3,7-inter-m-phenylene-4,5,6-trinor-3- oxa-9-deoxy-9,10-didehydro-PGD₁, a compound according to claim
 8. 11. A compound according to claim 5, wherein at least one of R₃ and R₄ is methyl.
 12. A compound according to claim 11, wherein R₃ and R₄ are both methyl.
 13. A compound according to claim 12, wherein R₅ is hydrogen.
 14. 2-Decarboxy-2-hydroxymethyl-16,16- dimethyl-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-9-deoxy- 9,10-didehydro-PGD₁, a compound according to claim
 13. 15. 2-Decarboxy-2-hydroxymethyl-16,16- dimethyl-15-epi-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa- 9-deoxy-9,10-didehydro-PGD₁, a compound according to claim
 13. 16. A compound according to claim 5, wherein R₃ and R₄ are both hydrogen.
 17. A compound according to claim 16, wherein R₅ is methyl.
 18. 2-Decarboxy-2-hydroxymethyl-15- methyl-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-9- deoxy-9,10-didehydro-PGD₁, a compound according to claim
 17. 19. 2-Decarboxy-2-hydroxymethyl-15-epi- 15-methyl-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa- 9-deoxy-9,10-didehydro-PGD₁, a compound according to claim
 17. 20. A compound according to claim 16, wherein R₅ is hydrogen.
 21. 2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-9-deoxy-9,10- didehydro-PGD₁, a compound according to claim
 20. 22. 2-Decarboxy-2-hydroxymethyl-15- epi-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-9-deoxy- 9,10-didehydro-9-deoxy-9,10-didehydro-PGD₁, a compound according to claim
 20. 